21979-55-5

Basic information

• Product Name: 3-bromo-1-methylquinolinium
• Synonyms: 3-Bromo-1-methylquinolinium; quinolinium, 3-bromo-1-methyl-
• CAS NO: 21979-55-5
• Molecular Formula: C₁₀H₉BrN*I
• Molecular Weight: 223.0886
• Mol File: 21979-55-5.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 3-bromo-1-methylquinolinium(CAS DataBase Reference)
• NIST Chemistry Reference: 3-bromo-1-methylquinolinium(21979-55-5)
• EPA Substance Registry System: 3-bromo-1-methylquinolinium(21979-55-5)

Safety Data

• Hazardous Substances Data: 21979-55-5(Hazardous Substances Data)

Usage

General Description

3-bromo-1-methylquinolinium is a chemical compound with the molecular formula C10H8BrN. It is a quinolinium salt with a bromine atom and a methyl group attached to the quinoline ring. 3-bromo-1-methylquinolinium can be used in organic synthesis as a reagent for various reactions, such as Suzuki coupling and Heck reaction. It is also used as a pharmaceutical intermediate in the synthesis of certain drugs. 3-bromo-1-methylquinolinium is a yellow to orange crystalline solid with low solubility in water, and it should be handled and stored with proper safety precautions due to its potential hazards as a chemical reagent.

Upstream product

• 5332-24-1 3-bromoquinoline 
• 74-88-4 methyl iodide 

Downstream Products

• 1258559-76-0 1-methyl-3-(p-methoxyphenylethynyl)quinolinium iodide 
• 1258559-78-2 1-methyl-3-(p-trifluoromethylphenylethynyl)quinolinium iodide 
• 941-91-3 3-bromo-1-methylquinolin-2(1H)-one 
• 16021-60-6 1-Methyl-1,2-dihydroquinoline 

Relevant articles and documents

Functionalization at C2, C3, and C4 of quinolines: Discovery of water-soluble betaine dyes of C3 quinolinium derivatives with solvatochromic and pH-sensitive properties

During functionalization at C2, C3, and C4 of quinoline, we came across a one-step metal free synthesis of C3 quinolinium derivatives of mesomeric betaine dyes. Some mesomeric betaine dyes had solvatochromic properties, and were sensitive to pH and solvates in the water. Certain betaine dyes had different properties in acidic and basic environments; the reversible interconversion between yellow (neutral or basic condition) and colorless (acidic condition) forms of the dye occurs by pH change. The changes in UV absorbance intensities of the dyes in the presence of cyclodextrins indicated the inclusion complex formation between cyclodextrins and dyes. The betaine dyes were partially dissolved in water due to the presence of positive and negative charges in the molecule. These betaine dyes did not exhibit cytotoxic activity, hence may be used in biological research.

Heteroaromatic cation-based chromophores: Synthesis and nonlinear optical properties of Alkynylazinium salts

A variety of alkynylazinium cationic (D-π-A+) chromophores were prepared in good yields by the reaction of bromoazinium (pyridinium, quinolinium, and isoquinolinium iodides) with alkynes under Sonogashira conditions. The analysis of the experimentally recorded spectra is supported by quantum chemical calculations using restricted configuration interaction and density functional methods. First-order hyperpolarizabilities of (D-π-A +) azinium-based cations as a new class of second-order nonlinear optical (NLO) chromophores were also studied by hyper-Rayleigh scattering experiments and computational procedures. Copyright

Regioselectivity of Hydride Transfer to and between NAD+ Analogues

The reaction of 1-methyl- or 1-benzylquinolinium compounds, also bearing an electron-withdrawing substituent in the 3-position, with NaBH4, gives mixtures of the corresponding 1,2-dihydroquinolines and 1,4-dihydroquinolines in which the 1,2-dihydro derivatives usually predominate.The 1,2-derivatives can be isolated.The 1,2-isomers react with the quinolinium salts, giving the 1,4-isomers and regenerating quinolinium salts.This bimolecular isomerization can be used to convert a mixture of isomers to the 1,4-isomer on a preparative scale. 3-Cyano-1,2-dihydro-1-methylquinoline also isomerizes to the 1,2-isomer in the crystalline solid.The major first product of NaBH4 reduction of 3-(aminocarbonyl)-1-benzylpyridinium ion is the 1,6-dihydro derivative.This also isomerizes to the 1,4-dihydro compound in the presence of the pyridinium ion.Reduction of quinolinium derivatives with Na2S2O4 or a dihydropyridine directly produces the 1,4-isomer predominantly.Reduction of 3-(aminocarbonyl)-1-benzylpyridinium ion with Na2S2O4 in D2O gives the 1,4-dihydro derivative, but 8percent of the deuterium is in the 2-position; presumably by reversible isomerization.This deuterium redistribution may have important consequences for the interpretation of isotope effects.